ATE156119T1 - 2-FORMYLPYRIDINE THIOSEMICARBAZONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTITUMOR AGENTS - Google Patents

2-FORMYLPYRIDINE THIOSEMICARBAZONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTITUMOR AGENTS

Info

Publication number
ATE156119T1
ATE156119T1 AT93401234T AT93401234T ATE156119T1 AT E156119 T1 ATE156119 T1 AT E156119T1 AT 93401234 T AT93401234 T AT 93401234T AT 93401234 T AT93401234 T AT 93401234T AT E156119 T1 ATE156119 T1 AT E156119T1
Authority
AT
Austria
Prior art keywords
hydrogen
preparation
antitumor agents
lower alkyl
thiosemicarbazone derivatives
Prior art date
Application number
AT93401234T
Other languages
German (de)
Inventor
Alan C Sartorelli
Tai-Shun Lin
Original Assignee
Univ Yale
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Yale filed Critical Univ Yale
Application granted granted Critical
Publication of ATE156119T1 publication Critical patent/ATE156119T1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention discloses the use of an active compound of the formula : <CHEM> wherein : either <a) R<1> is NHR<4>, NR<4>R<5> or OH and R<3> is hydrogen or <b) R<3> is NHR<4>, NR<4>R<5> or OH and R<1> is hydrogen ; R<2> is hydrogen or C1-4 lower alkyl ; R<4> is hydrogen, hydroxyl or C1-4 lower alkyl ; and R<5> is C1-4 lower alkyl ; provided that when R<1> is OH, R<2> is methyl, and provided that when R<3> is N(CH3)2 or OH, R<1> and R<2> cannot both be hydrogen or a pharmaceutically acceptable salt or hydrate thereof for the manufacture of a medicament for treating a tumor in a mammal, as well as new compounds, of the formula (I) except the compound wherein R<1> is OH, R<2> is methyl and R<3> is hydrogen and the corresponding pharmaceutical composition.
AT93401234T 1992-05-13 1993-05-13 2-FORMYLPYRIDINE THIOSEMICARBAZONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTITUMOR AGENTS ATE156119T1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/882,154 US5281715A (en) 1992-05-13 1992-05-13 2-formylpyridine thiosemicarbazone compounds

Publications (1)

Publication Number Publication Date
ATE156119T1 true ATE156119T1 (en) 1997-08-15

Family

ID=25379994

Family Applications (1)

Application Number Title Priority Date Filing Date
AT93401234T ATE156119T1 (en) 1992-05-13 1993-05-13 2-FORMYLPYRIDINE THIOSEMICARBAZONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTITUMOR AGENTS

Country Status (9)

Country Link
US (2) US5281715A (en)
EP (1) EP0570294B1 (en)
JP (1) JP3192027B2 (en)
AT (1) ATE156119T1 (en)
CA (1) CA2095881C (en)
DE (1) DE69312567T2 (en)
DK (1) DK0570294T3 (en)
ES (1) ES2108240T3 (en)
GR (1) GR3025207T3 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2065299C1 (en) * 1994-07-15 1996-08-20 Акционерное общество закрытого типа "Олвик" Nootropic and tranquilizing agent
US5767134A (en) * 1997-05-15 1998-06-16 Vion Pharmaceuticals, Inc. Prodrug forms of ribonucleotide reductase inhibitors 3-AP and 3-AMP
US6040338A (en) * 1997-11-03 2000-03-21 Yale University N,n-bis(sulfonyl)hydrazines useful as antineoplastic agents
CA2525298A1 (en) * 2003-05-01 2004-11-18 Panacea Pharmaceuticals, Inc. Methods of treating ischemic related conditions
CA2527799A1 (en) * 2003-05-30 2004-12-16 Merck & Co., Inc. Methods for identifying modulators of kinesin activity
US20060194810A1 (en) * 2004-04-30 2006-08-31 Bijan Almassian Methods of treating ischemic related conditions
US20090298891A1 (en) * 2005-09-16 2009-12-03 Government Of The Us, As Represented By The Secretady Of Health And Human Services Methods of Treating or Preventing Cancer Using Pyridine Carboxaldehyde Pyridine Thiosemicarbazone Radiosensitizing Agents
MD4126C1 (en) * 2010-11-15 2012-04-30 Государственный Университет Молд0 N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor
US20140271812A1 (en) * 2013-03-14 2014-09-18 Panacea Pharmaceuticals Treatment for chemotherapy-induced cognitive impairment
US20140287021A1 (en) 2013-03-21 2014-09-25 Panacea Pharmaceuticals Treatment of chemotherapy-induced peripheral neuropathy
MD4349C1 (en) * 2014-06-23 2015-12-31 Государственный Университет Молд0 N-(3-methoxyphenyl)-2-(pyridine-2-ylmethylene)-hydrazinecarbothioamide compound - inhibitor of human melanoma MeW-164 cell proliferation
MD4407C1 (en) * 2015-04-29 2016-10-31 Государственный Университет Молд0 Inhibitor of human myeloid leukemia HL-60 cells based on bis[N-(prop-2-en-1-yl)-2-(pyridine-2-ylmethylidene)hydrazinecarbothioamide]nickel(II) chloride hydrate
MD4393C1 (en) * 2015-09-04 2016-08-31 Государственный Университет Молд0 Inhibitor of human myeloid leukemia HL-60 cells based on nitrato-[N′-(1-pyridine-2-ylmethylidene)-morpholine-4-carbothiohydrazido(1-)]copper
MD4434C1 (en) * 2015-10-09 2017-04-30 Государственный Университет Молд0 Use of N'-[1-(2-pyridyl)ethylidene]morpholin-4-carbothiohydrazide as a human myeloid leukemia HL-60 cell proliferation inhibitor
MD4520C1 (en) * 2016-12-16 2018-05-31 Государственный Университет Молд0 N-(4-butoxyphenyl)-2-(pyridin-2-ylmethylidene)hydrazinecarbothioamide as T-47D breast cancer cells growth inhibitor
CN109265453A (en) * 2018-10-23 2019-01-25 华侨大学 It is a kind of as the semicarbazones analog derivative of caspase-3 activator and its application

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8320308D0 (en) * 1983-07-28 1983-09-01 Wellcome Found Antiviral combinations

Also Published As

Publication number Publication date
CA2095881A1 (en) 1993-11-14
ES2108240T3 (en) 1997-12-16
DE69312567D1 (en) 1997-09-04
JPH06128230A (en) 1994-05-10
DE69312567T2 (en) 1998-03-19
GR3025207T3 (en) 1998-02-27
US5281715A (en) 1994-01-25
EP0570294A1 (en) 1993-11-18
EP0570294B1 (en) 1997-07-30
US5721259A (en) 1998-02-24
CA2095881C (en) 2002-01-22
DK0570294T3 (en) 1998-02-02
JP3192027B2 (en) 2001-07-23

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Legal Events

Date Code Title Description
UEP Publication of translation of european patent specification
REN Ceased due to non-payment of the annual fee